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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 21.2, Problem 5P
Textbook Problem
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Predict the products of the following nucleophilic acyl substitution reactions:

Chapter 21.2, Problem 5P, Predict the products of the following nucleophilic acyl substitution reactions:

Interpretation Introduction

a)

Organic Chemistry, Chapter 21.2, Problem 5P , additional homework tip  1

Interpretation:

Predict the products of the nucleophilic acyl substitution reactions.

Concept introduction:

The nucleophilic acyl substitution reaction involved is Base Promoted hydrolysis, not, base catalysed, as shall be seen, because the base -OH is also the nucleophile that adds to the ester and forms part of the product. It participates in the reaction and is not regenerated later [implied in catalysis which does not occur here.]

Explanation of Solution

Steps 1 and 2 result in the rate determining addition of the nucleophile, -OH followed by the non-rate limiting elimination of the leaving group CH3. These two steps, which form the carboxylic acid, are reversible, because the stability a the reactants and products is comparable next, the carboxylic acid is a strong organic acid and the leaving group OCH3 is also a strong base, so and acid-base reaction occurs in step 3 to form the carboxylate anion.

The carboxylate anion is resonance stabilized, and this drives the equilibrium in its favour...

Interpretation Introduction

b)

Organic Chemistry, Chapter 21.2, Problem 5P , additional homework tip  2

Interpretation:

Predict the products of the nucleophilic acyl substitution reactions.

Concept introduction:

To predict the product of a nucleophilic acyl substitution, replace the leaving group of the reagent [viz acetyl chloride ie chloride cl- by the nucleophilic fragment -NH2] to get the actual product.

To bit these in to the context of reaction b the following mechanism is devised.

Interpretation Introduction

c)

Organic Chemistry, Chapter 21.2, Problem 5P , additional homework tip  3

Interpretation:

Predict the products of the nucleophilic acyl substitution reactions.

Interpretation Introduction

d)

Organic Chemistry, Chapter 21.2, Problem 5P , additional homework tip  4

Interpretation:

Predict the products of the nucleophilic acyl substitution reactions.

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Chapter 21 Solutions

Organic Chemistry
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Ch. 21.4 - Write the mechanism of the reaction just shown...Ch. 21.4 - How could you prepare the following amides using...Ch. 21.4 - How could you prepare the following ketones by...Ch. 21.5 - Write the mechanism of the reaction between...Ch. 21.5 - What product would you expect from reaction of one...Ch. 21.6 - Why is the saponification of an ester...Ch. 21.6 - What product would you expect from the reaction of...Ch. 21.6 - Show the products you would obtain by reduction of...Ch. 21.6 - What ester and what Grignard reagent might you...Ch. 21.7 - How would you convert N-ethylbenzamide to each of...Ch. 21.7 - How would you use the reaction of an amide with...Ch. 21.8 - Write the mechanism of the reaction shown in...Ch. 21.9 - Draw structures of the step-growth polymers you...Ch. 21.9 - Kevlar, a nylon polymer prepared by reaction of...Ch. 21.SE - Name the following compounds:Ch. 21.SE - How would you prepare the following compounds...Ch. 21.SE - The following structure represents a tetrahedral...Ch. 21.SE - Electrostatic potential maps of a typical amide...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the complete...Ch. 21.SE - Pivalic mixed anhydrides are often used to form...Ch. 21.SE - When 4-dimethylaminopyridine (DMAP) is added in...Ch. 21.SE - Fats are biosynthesized from glycerol 3-phosphate...Ch. 21.SE - Treatment of an -amino acid with DCC yields a...Ch. 21.SE - Succinic anhydride yields the cyclic imide...Ch. 21.SE - The hydrolysis of a biological thioester to the...Ch. 21.SE - One step in the gluconeogenesis pathway for the...Ch. 21.SE - Bacteria typically develop a resistance to...Ch. 21.SE - The following reaction, called the benzilic acid...Ch. 21.SE - In the iodoform reaction, a triiodomethyl ketone...Ch. 21.SE - Give IUPAC names for the following compounds:Ch. 21.SE - Draw structures corresponding to the following...Ch. 21.SE - Draw and name compounds that meet the following...Ch. 21.SE - Predict the product, if any, of reaction between...Ch. 21.SE - Answer Problem 21-48 for reaction of the listed...Ch. 21.SE - Answer Problem 21-48 for reaction of the listed...Ch. 21.SE - What product would you expect to obtain from...Ch. 21.SE - How might you prepare the following compounds from...Ch. 21.SE - Predict the product(s) of the following reactions:Ch. 21.SE - The following reactivity order has been found for...Ch. 21.SE - Explain the observation that attempted Fischer...Ch. 21.SE - Outline methods for the preparation of...Ch. 21.SE - Treatment of 5-aminopentanoic acid with DCC...Ch. 21.SE - When ethyl benzoate is heated in methanol...Ch. 21.SE - tert-Butoxycarbonyl azide, a reagent used in...Ch. 21.SE - The step-growth polymer nylon 6 is prepared from...Ch. 21.SE - Qiana, a polyamide fiber with a silky texture, has...Ch. 21.SE - What is the structure of the polymer produced by...Ch. 21.SE - Polyimides with the structure shown are used as...Ch. 21.SE - How would you distinguish spectroscopically...Ch. 21.SE - Propose a structure for a compound, C4H7ClO2, that...Ch. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - The following reactivity order has been found for...Ch. 21.SE - When a carboxylic acid is dissolved in...Ch. 21.SE - We said in Section 21-6 that mechanistic studies...Ch. 21.SE - Treatment of a carboxylic acid with...Ch. 21.SE - Butacetin is an analgesic (pain-killing) agent...Ch. 21.SE - Phenyl 4-aminosalicylate is a drug used in the...Ch. 21.SE - N,N-Diethyl-m-toluamide (DEET) is the active...Ch. 21.SE - Tranexamic acid, a drug useful against blood...Ch. 21.SE - One frequently used method for preparing methyl...Ch. 21.SE - Draw the structure of the polymer you would expect...Ch. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Propose structures for compounds with the...Ch. 21.SE - Propose a structure for the compound with the...Ch. 21.SE - Draw the structure of the compound that produced...Ch. 21.SE - When an amide is formed from an acid chloride or...Ch. 21.SE - Epoxy adhesives are prepared in two steps. SN2...

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